TWI338696B - Atrp polymers with structurally modified terminal groups from lubricant or polymer additives - Google Patents

Info

Publication number

TWI338696B

TWI338696B TW092112307A TW92112307A TWI338696B TW I338696 B TWI338696 B TW I338696B TW 092112307 A TW092112307 A TW 092112307A TW 92112307 A TW92112307 A TW 92112307A TW I338696 B TWI338696 B TW I338696B

Authority

TW

Taiwan

Prior art keywords

alkyl

group

polymer

acrylic acid

acid

Prior art date

2002-05-08

Links

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• 229920000642 polymer Polymers 0.000 title claims abstract description 147
• 239000000654 additive Substances 0.000 title claims abstract description 33
• 239000000314 lubricant Substances 0.000 title claims abstract description 21
• 239000000203 mixture Substances 0.000 claims abstract description 59
• 238000010560 atom transfer radical polymerization reaction Methods 0.000 claims abstract description 33
• 239000003963 antioxidant agent Substances 0.000 claims abstract description 25
• 230000000996 additive effect Effects 0.000 claims abstract description 18
• 239000003112 inhibitor Substances 0.000 claims abstract description 9
• 238000005260 corrosion Methods 0.000 claims abstract description 8
• 230000015556 catabolic process Effects 0.000 claims abstract description 7
• 230000007797 corrosion Effects 0.000 claims abstract description 7
• 238000006731 degradation reaction Methods 0.000 claims abstract description 7
• 239000006078 metal deactivator Substances 0.000 claims abstract description 7
• -1 C5-C8% Chemical group 0.000 claims description 124
• 125000000217 alkyl group Chemical group 0.000 claims description 108
• NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 84
• SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 55
• 239000000178 monomer Substances 0.000 claims description 33
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 28
• 239000002253 acid Substances 0.000 claims description 28
• 239000002585 base Substances 0.000 claims description 24
• 239000003999 initiator Substances 0.000 claims description 23
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 22
• 239000005977 Ethylene Substances 0.000 claims description 22
• 238000006116 polymerization reaction Methods 0.000 claims description 22
• 125000005907 alkyl ester group Chemical group 0.000 claims description 21
• 150000001875 compounds Chemical class 0.000 claims description 21
• 229910052739 hydrogen Inorganic materials 0.000 claims description 20
• 239000003795 chemical substances by application Substances 0.000 claims description 19
• LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 19
• 150000002148 esters Chemical class 0.000 claims description 18
• 239000001257 hydrogen Substances 0.000 claims description 17
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
• 230000003078 antioxidant effect Effects 0.000 claims description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
• 125000003545 alkoxy group Chemical group 0.000 claims description 15
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 15
• 239000003505 polymerization initiator Substances 0.000 claims description 15
• 150000001412 amines Chemical class 0.000 claims description 13
• 125000001424 substituent group Chemical group 0.000 claims description 13
• 125000003118 aryl group Chemical group 0.000 claims description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
• 229910052736 halogen Inorganic materials 0.000 claims description 12
• 230000003647 oxidation Effects 0.000 claims description 12
• 238000007254 oxidation reaction Methods 0.000 claims description 12
• 125000005250 alkyl acrylate group Chemical group 0.000 claims description 11
• 239000012634 fragment Substances 0.000 claims description 11
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 10
• 229910052717 sulfur Inorganic materials 0.000 claims description 10
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
• 125000004185 ester group Chemical group 0.000 claims description 9
• 125000000524 functional group Chemical group 0.000 claims description 9
• 150000002367 halogens Chemical group 0.000 claims description 9
• 235000021419 vinegar Nutrition 0.000 claims description 9
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
• 229910052799 carbon Inorganic materials 0.000 claims description 8
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
• 229910052760 oxygen Inorganic materials 0.000 claims description 8
• 239000001301 oxygen Substances 0.000 claims description 8
• QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 8
• 239000011593 sulfur Substances 0.000 claims description 8
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
• WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 7
• 230000001050 lubricating effect Effects 0.000 claims description 7
• 235000019260 propionic acid Nutrition 0.000 claims description 7
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 7
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 7
• 238000010526 radical polymerization reaction Methods 0.000 claims description 7
• 239000000052 vinegar Substances 0.000 claims description 7
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Natural products OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 6
• 239000002199 base oil Substances 0.000 claims description 6
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 6
• 150000002431 hydrogen Chemical class 0.000 claims description 6
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 6
• 229920002554 vinyl polymer Polymers 0.000 claims description 6
• 229910019142 PO4 Inorganic materials 0.000 claims description 5
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
• 150000001768 cations Chemical class 0.000 claims description 5
• 235000021317 phosphate Nutrition 0.000 claims description 5
• AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 5
• KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 4
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 4
• 125000002947 alkylene group Chemical group 0.000 claims description 4
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
• 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 4
• 229910052707 ruthenium Inorganic materials 0.000 claims description 4
• 238000012360 testing method Methods 0.000 claims description 4
• SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 claims description 3
• 229930185605 Bisphenol Natural products 0.000 claims description 3
• CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical group CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 3
• ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 3
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
• RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical class OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 claims description 3
• 230000004913 activation Effects 0.000 claims description 3
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 229910000071 diazene Inorganic materials 0.000 claims description 3
• 239000001530 fumaric acid Substances 0.000 claims description 3
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
• 239000011976 maleic acid Substances 0.000 claims description 3
• LCAGMECBZMHMCD-UHFFFAOYSA-N 2-tert-butyl-2-(4-hydroxyphenyl)-3,3-dimethylbutanoic acid Chemical compound CC(C)(C)C(C(O)=O)(C(C)(C)C)C1=CC=C(O)C=C1 LCAGMECBZMHMCD-UHFFFAOYSA-N 0.000 claims description 2
• ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical class C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 claims description 2
• LBSXSAXOLABXMF-UHFFFAOYSA-N 4-Vinylaniline Chemical group NC1=CC=C(C=C)C=C1 LBSXSAXOLABXMF-UHFFFAOYSA-N 0.000 claims description 2
• 229910052783 alkali metal Inorganic materials 0.000 claims description 2
• 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
• 210000000988 bone and bone Anatomy 0.000 claims description 2
• 239000000470 constituent Substances 0.000 claims description 2
• RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 claims description 2
• RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims description 2
• 150000002500 ions Chemical class 0.000 claims description 2
• GMTCPFCMAHMEMT-UHFFFAOYSA-N n-decyldecan-1-amine Chemical compound CCCCCCCCCCNCCCCCCCCCC GMTCPFCMAHMEMT-UHFFFAOYSA-N 0.000 claims description 2
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 2
• XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 2
• 239000002685 polymerization catalyst Substances 0.000 claims description 2
• 239000002689 soil Substances 0.000 claims description 2
• 150000003573 thiols Chemical class 0.000 claims description 2
• 150000003852 triazoles Chemical class 0.000 claims description 2
• 150000001350 alkyl halides Chemical class 0.000 claims 2
• DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims 2
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
• VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims 1
• 150000000183 1,3-benzoxazoles Chemical class 0.000 claims 1
• KVGZZAHHUNAVKZ-UHFFFAOYSA-N 1,4-Dioxin Chemical compound O1C=COC=C1 KVGZZAHHUNAVKZ-UHFFFAOYSA-N 0.000 claims 1
• QHVBLSNVXDSMEB-UHFFFAOYSA-N 2-(diethylamino)ethyl prop-2-enoate Chemical compound CCN(CC)CCOC(=O)C=C QHVBLSNVXDSMEB-UHFFFAOYSA-N 0.000 claims 1
• DAWJJMYZJQJLPZ-UHFFFAOYSA-N 2-sulfanylprop-2-enoic acid Chemical compound OC(=O)C(S)=C DAWJJMYZJQJLPZ-UHFFFAOYSA-N 0.000 claims 1
• KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 claims 1
• HSGHXTINOVTZFT-UHFFFAOYSA-N C(C(=C)C)(=O)OCCN(C(N)=N)C(N)=N Chemical compound C(C(=C)C)(=O)OCCN(C(N)=N)C(N)=N HSGHXTINOVTZFT-UHFFFAOYSA-N 0.000 claims 1
• 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
• CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 1
• 239000003513 alkali Substances 0.000 claims 1
• 150000001340 alkali metals Chemical class 0.000 claims 1
• 150000001502 aryl halides Chemical class 0.000 claims 1
• UDEWPOVQBGFNGE-UHFFFAOYSA-N benzoic acid n-propyl ester Natural products CCCOC(=O)C1=CC=CC=C1 UDEWPOVQBGFNGE-UHFFFAOYSA-N 0.000 claims 1
• QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims 1
• 239000012964 benzotriazole Substances 0.000 claims 1
• 125000004093 cyano group Chemical group *C#N 0.000 claims 1
• GTBGXKPAKVYEKJ-UHFFFAOYSA-N decyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C(C)=C GTBGXKPAKVYEKJ-UHFFFAOYSA-N 0.000 claims 1
• FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical group CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims 1
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
• 239000008267 milk Substances 0.000 claims 1
• 229910052762 osmium Inorganic materials 0.000 claims 1
• SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims 1
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 1
• WHFQAROQMWLMEY-UHFFFAOYSA-N propylene dimer Chemical group CC=C.CC=C WHFQAROQMWLMEY-UHFFFAOYSA-N 0.000 claims 1
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 1
• 229920001400 block copolymer Polymers 0.000 abstract description 14
• 239000005069 Extreme pressure additive Substances 0.000 abstract description 2
• 239000007866 anti-wear additive Substances 0.000 abstract description 2
• 230000001590 oxidative effect Effects 0.000 abstract description 2
• 101710141544 Allatotropin-related peptide Proteins 0.000 abstract 1
• 229920001577 copolymer Polymers 0.000 description 38
• 238000000034 method Methods 0.000 description 26
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
• 239000007789 gas Substances 0.000 description 18
• 235000006708 antioxidants Nutrition 0.000 description 17
• 229910052751 metal Inorganic materials 0.000 description 17
• 239000002184 metal Substances 0.000 description 17
• 239000003921 oil Substances 0.000 description 16
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
• 239000012530 fluid Substances 0.000 description 15
• 235000019198 oils Nutrition 0.000 description 15
• 239000003054 catalyst Substances 0.000 description 14
• 150000003254 radicals Chemical class 0.000 description 14
• 239000002904 solvent Substances 0.000 description 14
• 238000007792 addition Methods 0.000 description 12
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 11
• 238000006243 chemical reaction Methods 0.000 description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
• 239000000243 solution Substances 0.000 description 10
• 239000003446 ligand Substances 0.000 description 9
• 229920000768 polyamine Polymers 0.000 description 9
• 229920002857 polybutadiene Polymers 0.000 description 9
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 8
• 239000005062 Polybutadiene Substances 0.000 description 8
• 239000010949 copper Substances 0.000 description 8
• 239000011541 reaction mixture Substances 0.000 description 8
• 238000012546 transfer Methods 0.000 description 8
• 239000004743 Polypropylene Substances 0.000 description 7
• 239000004793 Polystyrene Substances 0.000 description 7
• ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 7
• XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 7
• 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 7
• 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 7
• 239000010687 lubricating oil Substances 0.000 description 7
• 239000000463 material Substances 0.000 description 7
• 229920002223 polystyrene Polymers 0.000 description 7
• 150000003839 salts Chemical class 0.000 description 7
• 229910052723 transition metal Inorganic materials 0.000 description 7
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
• 125000003277 amino group Chemical group 0.000 description 6
• 238000005555 metalworking Methods 0.000 description 6
• 230000008569 process Effects 0.000 description 6
• 239000000047 product Substances 0.000 description 6
• 239000000126 substance Substances 0.000 description 6
• 150000003624 transition metals Chemical class 0.000 description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
• 239000004721 Polyphenylene oxide Substances 0.000 description 5
• 125000004429 atom Chemical group 0.000 description 5
• 239000012043 crude product Substances 0.000 description 5
• 229920001971 elastomer Polymers 0.000 description 5
• 238000000921 elemental analysis Methods 0.000 description 5
• 239000000839 emulsion Substances 0.000 description 5
• 239000003925 fat Substances 0.000 description 5
• 235000019197 fats Nutrition 0.000 description 5
• 239000000446 fuel Substances 0.000 description 5
• 229930195733 hydrocarbon Natural products 0.000 description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
• 239000002480 mineral oil Substances 0.000 description 5
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
• 229920006324 polyoxymethylene Polymers 0.000 description 5
• 229920001155 polypropylene Polymers 0.000 description 5
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
• 125000003396 thiol group Chemical group [H]S* 0.000 description 5
• AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
• PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 4
• 229920000877 Melamine resin Polymers 0.000 description 4
• 239000004698 Polyethylene Substances 0.000 description 4
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
• 229920002125 Sokalan® Polymers 0.000 description 4
• 150000001335 aliphatic alkanes Chemical class 0.000 description 4
• 150000001450 anions Chemical class 0.000 description 4
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
• 229910052794 bromium Inorganic materials 0.000 description 4
• 239000001913 cellulose Substances 0.000 description 4
• 229920002678 cellulose Polymers 0.000 description 4
• 239000006184 cosolvent Substances 0.000 description 4
• 230000000694 effects Effects 0.000 description 4
• 150000002170 ethers Chemical class 0.000 description 4
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
• 239000005038 ethylene vinyl acetate Substances 0.000 description 4
• 150000002334 glycols Chemical class 0.000 description 4
• 229920001519 homopolymer Polymers 0.000 description 4
• 150000002430 hydrocarbons Chemical class 0.000 description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
• KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 4
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
• 230000007935 neutral effect Effects 0.000 description 4
• 150000002923 oximes Chemical class 0.000 description 4
• 229910052698 phosphorus Inorganic materials 0.000 description 4
• 229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 4
• 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 4
• 239000004584 polyacrylic acid Substances 0.000 description 4
• 239000004417 polycarbonate Substances 0.000 description 4
• 229920000647 polyepoxide Polymers 0.000 description 4
• 229920000728 polyester Polymers 0.000 description 4
• 229920000570 polyether Polymers 0.000 description 4
• 229920000915 polyvinyl chloride Polymers 0.000 description 4
• 238000002360 preparation method Methods 0.000 description 4
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